Most marketing is still selling the SUV driver racing across open terrain, while the actual buyer is dodging potholes in Brooklyn. In this episode, Shann and Lynette dig into one of advertising's oldest questions: when does the fantasy work, and when does it backfire? They trace the line from menopause ads featuring 20-year-olds to period products using blue liquid, and argue that the answer has a lot to do with whether you're selling something that signals identity to others or something that just has to work. Plus: why one in two women still feel misunderstood by brands — despite a trillion dollars of advertising aimed at them.